Methyl 5,5'-difluoro-2'-nitrobiphenyl-2-carboxylate → 2,9-Difluoro-5-hydroxyphenanthridin-6(5H)-one

HRID 238074Notes

Reaction equation

HRID 238074 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=2[N+:15]([O-])=[O:16])[C:5]([C:18]([O:20]C)=O)=[CH:4][CH:3]=1.[H][H]>[Pd].CO>[F:14][C:12]1[CH:11]=[CH:10][C:9]2[N:15]([OH:16])[C:18](=[O:20])[C:5]3[C:6](=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:8]=2[CH:13]=1

Participants

5

Reactant 2

HCID 67296874Methyl 5,5'-difluoro-2'-nitrobiphenyl-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 672968652,9-Difluoro-5-hydroxyphenanthridin-6(5H)-oneYield 18.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the product of Example 38a (279.8 mg) was added methanol (7.5 mL) and 10% palladium on carbon (76 mg, 0.071 mmol). The flask was fitted with a hydrogen balloon and the mixture was de-gased and back-filled with hydrogen three times. The mixture was stirred under hydrogen for 16 h, diluted with dimethylformamide and filtered. The filtrate was concentrated to give a red solid. This material was triturated with dichloromethane/hexane (9/1) and filtered to provide the title compound (Example 38b, 43.15 mg, 0.175 mmol, quantitative yield).

Workup

  1. customthe mixture was de-gased
  2. additionback-filled with hydrogen three times
  3. additiondiluted with dimethylformamide
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customto give a red solid
  7. customThis material was triturated with dichloromethane/hexane (9/1)
  8. filtrationfiltered

Sources & evidence

ORD record
ord-8f3e3f794b5f4a708346305387e0bc98
Source dataset
uspto-grants-2014_02
Patent number
US08642538B2

Reaction notes

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